Acetic Acid Mixture with Hydrobromic Acid → HCID 53889850, compound

HRID 280966Notes

Reaction equation

HRID 280966 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([NH:28][C@@H:29]2[C:35](=[O:36])[N:34]([CH2:37][C:38]([O:40]C(C)(C)C)=[O:39])[C:33]3[CH:45]=[CH:46][CH:47]=[CH:48][C:32]=3[O:31][CH2:30]2)[C:23]([O:25]CC)=[O:24])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.Br.C(O)(=O)C>C(O)(=O)C.C(OCC)C>[C:23]([C@@H:22]([NH:28][C@@H:29]1[C:35](=[O:36])[N:34]([CH2:37][C:38]([OH:40])=[O:39])[C:33]2[CH:45]=[CH:46][CH:47]=[CH:48][C:32]=2[O:31][CH2:30]1)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)([OH:25])=[O:24]

Participants

5

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 54149894HCID 54149894, compound

Product 1

HCID 53889850HCID 53889850, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of tert-butyl 3(S)-[6-(1-benzyloxycarbonyl-4-piperidyl)-1(S)-ethoxycarbonylhexyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate (0.5 g) in acetic acid (1 ml) is added 30% hydrogen bromide-acetic acid solution (2 ml). The resulting mixture is allowed to stand for 1 hour at room temperature and then diluted with ethyl ether (100 ml). The supernatant layer is removed by decantation and the precipitate is dissolved in 1N sodium hydroxide solution (20 ml). The solution is allowed to stand for 30 minutes at room temperature. After addition of acetic acid (4 ml), the mixture is chromatographed on MCI gel using water-methanol (1:2) as an eluent. The eluate is concentrated in vacuo and lyophilized to give 3(S)-[1(S)-carboxy-6-(4-piperidyl)hexyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetic acid (0.23 g) as colorless powder.

Workup

  1. customThe supernatant layer is removed by decantation
  2. dissolutionthe precipitate is dissolved in 1N sodium hydroxide solution (20 ml)
  3. waitto stand for 30 minutes at room temperature
  4. additionAfter addition of acetic acid (4 ml)
  5. customthe mixture is chromatographed on MCI gel
  6. concentrationThe eluate is concentrated in vacuo

Sources & evidence

ORD record
ord-e81140c2028040929d637f8e0201d296
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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